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Phenothiazine coumarin-based pyridine salt compound as well as preparation and application thereof

A salt compound, coumarin technology, applied in chemical instruments and methods, organic chemistry, instruments, etc., can solve the problems of low detection limit, poor water solubility, low sensitivity of HOCl fluorescent probe, etc., and achieve good biocompatibility Sexuality, the effect of improving water solubility

Pending Publication Date: 2022-03-11
THE AFFILIATED HOSPITAL OF SOUTHWEST MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The object of the present invention is to provide a kind of phenothiazine coumarin base pyridinium salt compound and its preparation and application, solve the problem of low sensitivity and poor water solubility of existing HOCl fluorescent probe, the phenothiazine coumarin The water solubility of base pyridinium salt compounds is improved, and the detection limit is low, and the emission wavelength is also conducive to biological imaging

Method used

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  • Phenothiazine coumarin-based pyridine salt compound as well as preparation and application thereof
  • Phenothiazine coumarin-based pyridine salt compound as well as preparation and application thereof
  • Phenothiazine coumarin-based pyridine salt compound as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] A phenothiazine coumarinyl pyridinium salt compound, the preparation process of which is as follows:

[0038] (1) Synthesis of Intermediate 1

[0039]

[0040] Iodoethane (3.9g, 25mmol) and 2-methoxyphenothiazine (2.29g, 10mmol) were dissolved in 20mL of dimethyl sulfoxide, then NaOH (0.8g, 20mmol) was added, and the temperature was raised to 65°C for 15 Hour. After the reaction was completed, cool to room temperature, add 300mL of water, add dichloromethane (50mL×2) for extraction, wash with saturated brine (50mL×2), dry over anhydrous sodium sulfate, then remove the solvent under reduced pressure, and use the obtained residue with Separation on a 200-300 mesh silica gel column gave a white solid (2.3 g, 89.5%).

[0041] 1 H NMR (600MHz, DMSO-d 6 )δ7.14 (ddd, J=8.4, 7.2, 1.4Hz, 1H), 7.08 (dd, J=7.6, 1.7Hz, 1H), 7.02–6.94 (m, 2H), 6.92–6.86 (m, 1H) ,6.51(d,J=7.6Hz,2H),3.87(q,J=6.9Hz,2H),3.70(s,3H),1.25(t,J=6.9Hz,3H).

[0042] (2) Synthesis of compound 5

[004...

experiment example 1

[0061] The selectivity test of experimental example 1 to HOCl

[0062] Prepare the test solution of compound 5 (PBS:EtOH=8:2, V / V, 10μmol / L), take 3mL and transfer it to a quartz cuvette, add different types of active substances, stir slightly for 10s, and test its fluorescence ll.

[0063] Such as image 3 As shown, it is the selectivity test result of compound 5 in Example 1 of the present invention to HOCl, the excitation wavelength is 420nm, image 3 The illustration in is the white light diagram and fluorescence diagram of the compound 5 solution under the action of various active substances, the ordinate I 570 Indicates the emission intensity of compound 5 at 570 nm. The results showed that compound 5 had excellent selectivity to HOCl.

experiment example 2

[0064] Experimental Example 2 Fluorescence intensity test of different concentrations of HOCl

[0065] Prepare the test solution of compound 5 (PBS:EtOH=8:2, V / V, 10μmol / L), take 3mL and transfer it to a quartz cuvette, gradually add HOCl solution dropwise, stir gently for 10s, and test its fluorescence emission spectrum .

[0066] Such as Figure 4 Shown is the fluorescence titration diagram of compound 5 in Example 1 of the present invention against HOCl, and the excitation wavelength is 420nm. Such as Figure 5 Shown is the fluorescence response of compound 5 in Example 1 of the present invention to a low concentration of HOCl, from which the detection limit of compound 5 to HOCl is calculated to be 970pM. The results showed that the detection sensitivity of compound 5 to HOCl was very high.

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Abstract

The invention discloses a phenothiazine coumarin-based pyridine salt compound and preparation and application thereof, the chemical structural formula of the compound is as shown in formula (I), in the formula (I), R1 and R2 are independently selected from C1-C12 saturated alkanes; x is selected from halogen. According to the phenothiazine coumarin-based pyridine salt compound disclosed by the invention, pyridinium salt is introduced to the 3-site of phenothiazine coumarin, so that the water solubility of the compound is improved, the emission wavelength is 530-610nm, the optimal emission wavelength is 570nm, and bioimaging is more facilitated. Moreover, in the reported phenothiazine coumarin HOCl fluorescent probes, the detection limit of the probe disclosed by the invention on HOCl is the lowest. Besides, under the condition that no exogenous stimulus is added, the probe disclosed by the invention can effectively distinguish normal cells from tumor cells, and has good biocompatibility.

Description

technical field [0001] The invention relates to a pyridinium salt compound, in particular to a phenothiazinecoumarinyl pyridinium salt compound and its preparation and application. Background technique [0002] HOCl is a kind of reactive oxygen species produced endogenously by cells, which is obtained by the reaction of hydrogen peroxide and chloride ions catalyzed by myeloperoxidase. Under normal circumstances, HOCl plays the role of a guardian in the biological system, can kill bacteria and anti-virus, and participate in the immune system in the body. However, in some pathophysiological processes, the concentration of HOCl is often too high, causing irreversible damage to the structure of biological macromolecules, thereby affecting cell functions, and even leading to cell apoptosis. For example, the concentration of HOCl in tumor cells is higher than that in normal cells. Taking advantage of this feature, highly sensitive probes for HOCl can be developed to achieve effe...

Claims

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Application Information

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IPC IPC(8): C07D513/04C09K11/06G01N21/64
CPCC07D513/04C09K11/06G01N21/6428C09K2211/1037C09K2211/1029G01N2021/6443
Inventor 后际挺任文秀袁凤英王冰雅
Owner THE AFFILIATED HOSPITAL OF SOUTHWEST MEDICAL UNIV
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